Novel polycarboxylate porphyrins: synthesis, characterization, photophysical properties and preliminary antimicrobial study against Gram-positive bacteria

Bioorg Med Chem Lett. 2015 Jan 15;25(2):355-62. doi: 10.1016/j.bmcl.2014.11.033. Epub 2014 Nov 18.

Abstract

We describe the synthesis, characterization and photophysical properties of two new polycarboxylic photosensitizers. Owing to their structural design, these two compounds show water solubilities larger than natural carboxylic photosensitizers (e.g., protoporphyrin IX, hematoporphyrin, etc.) and also good singlet oxygen quantum yields. These compounds were tested as photo-antimicrobial agents against Staphylococcus aureus and Bacillus cereus strains. Results reveal that their photocytotoxicities are strongly dependent on their amphiphilic character and more precisely the number and position of the carboxylic acid and mesityl substituents.

Keywords: Antibacterial agents; Carboxylic porphyrins; Oxygen singlet quantum yield; Photodynamic antimicrobial chemotherapy; Photosensitizers.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Bacterial Agents / chemical synthesis*
  • Anti-Bacterial Agents / pharmacology*
  • Carboxylic Acids / chemistry*
  • Gram-Positive Bacteria / drug effects*
  • Gram-Positive Bacteria / growth & development
  • Gram-Positive Bacterial Infections / drug therapy*
  • Gram-Positive Bacterial Infections / microbiology
  • Humans
  • Light
  • Microbial Sensitivity Tests
  • Models, Molecular
  • Molecular Structure
  • Photochemistry
  • Photosensitizing Agents / chemical synthesis
  • Photosensitizing Agents / pharmacology*
  • Porphyrins / chemical synthesis
  • Porphyrins / pharmacology*
  • Singlet Oxygen / chemistry
  • Structure-Activity Relationship

Substances

  • Anti-Bacterial Agents
  • Carboxylic Acids
  • Photosensitizing Agents
  • Porphyrins
  • Singlet Oxygen